UA94003C2 - Соединения бензоилпиразола, гербицид ha их ochobe и способ борьбы c нежелательными растениями - Google Patents

Info

Publication number

UA94003C2

UA94003C2 UAA200905260A UAA200905260A UA94003C2 UA 94003 C2 UA94003 C2 UA 94003C2 UA A200905260 A UAA200905260 A UA A200905260A UA A200905260 A UAA200905260 A UA A200905260A UA 94003 C2 UA94003 C2 UA 94003C2

Authority

UA

Ukraine

Prior art keywords

methyl

formula

alkyl

reaction

compounds

Prior art date

2006-11-28

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• 230000002363 herbicidal effect Effects 0.000 title claims abstract description 35
• 238000000034 method Methods 0.000 title claims abstract description 28
• 239000004009 herbicide Substances 0.000 title claims abstract description 20
• UYMQWGLCXYHTES-UHFFFAOYSA-N phenyl(1h-pyrazol-5-yl)methanone Chemical class C=1C=CC=CC=1C(=O)C1=CC=NN1 UYMQWGLCXYHTES-UHFFFAOYSA-N 0.000 title description 6
• -1 benzoylpyrazole compound Chemical class 0.000 claims abstract description 147
• 150000003839 salts Chemical class 0.000 claims abstract description 31
• 239000004480 active ingredient Substances 0.000 claims abstract description 11
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 4
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
• 125000000217 alkyl group Chemical group 0.000 abstract description 19
• 238000004519 manufacturing process Methods 0.000 abstract description 15
• 239000002689 soil Substances 0.000 abstract description 13
• 150000002367 halogens Chemical class 0.000 abstract description 9
• 125000003545 alkoxy group Chemical group 0.000 abstract description 8
• 229910052736 halogen Inorganic materials 0.000 abstract description 8
• 125000004438 haloalkoxy group Chemical group 0.000 abstract description 5
• 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract description 3
• 125000002947 alkylene group Chemical group 0.000 abstract description 3
• 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
• 150000001875 compounds Chemical class 0.000 description 137
• 238000006243 chemical reaction Methods 0.000 description 93
• 239000002904 solvent Substances 0.000 description 67
• 241000196324 Embryophyta Species 0.000 description 46
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
• 239000002585 base Substances 0.000 description 26
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
• 239000000203 mixture Substances 0.000 description 20
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 16
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
• 244000062793 Sorghum vulgare Species 0.000 description 15
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
• 229920003171 Poly (ethylene oxide) Polymers 0.000 description 14
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 13
• 235000019713 millet Nutrition 0.000 description 13
• 238000002360 preparation method Methods 0.000 description 13
• 239000011734 sodium Substances 0.000 description 13
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
• 229910052708 sodium Inorganic materials 0.000 description 12
• 240000008042 Zea mays Species 0.000 description 11
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 11
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 11
• 235000005822 corn Nutrition 0.000 description 11
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
• 240000007594 Oryza sativa Species 0.000 description 10
• 235000007164 Oryza sativa Nutrition 0.000 description 10
• 239000003054 catalyst Substances 0.000 description 10
• 230000002829 reductive effect Effects 0.000 description 10
• 235000009566 rice Nutrition 0.000 description 10
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
• 235000014113 dietary fatty acids Nutrition 0.000 description 9
• 239000000194 fatty acid Substances 0.000 description 9
• 229930195729 fatty acid Natural products 0.000 description 9
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
• NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
• 230000009036 growth inhibition Effects 0.000 description 8
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
• 239000000843 powder Substances 0.000 description 8
• 230000035484 reaction time Effects 0.000 description 8
• OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 7
• 239000002253 acid Substances 0.000 description 7
• 239000000654 additive Substances 0.000 description 7
• 239000012141 concentrate Substances 0.000 description 7
• 239000000839 emulsion Substances 0.000 description 7
• 150000007529 inorganic bases Chemical class 0.000 description 7
• 150000007530 organic bases Chemical class 0.000 description 7
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
• 238000005481 NMR spectroscopy Methods 0.000 description 6
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• 229910052783 alkali metal Inorganic materials 0.000 description 6
• 150000002148 esters Chemical class 0.000 description 6
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
• 239000002798 polar solvent Substances 0.000 description 6
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
• HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 6
• 239000008096 xylene Substances 0.000 description 6
• UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 5
• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 5
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 5
• 241000287828 Gallus gallus Species 0.000 description 5
• 241000219098 Parthenocissus Species 0.000 description 5
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 5
• KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 5
• 150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
• 230000015572 biosynthetic process Effects 0.000 description 5
• 239000003795 chemical substances by application Substances 0.000 description 5
• LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
• 150000004665 fatty acids Chemical class 0.000 description 5
• 150000008282 halocarbons Chemical class 0.000 description 5
• YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 5
• 239000012044 organic layer Substances 0.000 description 5
• 239000011591 potassium Substances 0.000 description 5
• 229910052700 potassium Inorganic materials 0.000 description 5
• 229960003975 potassium Drugs 0.000 description 5
• 229940090181 propyl acetate Drugs 0.000 description 5
• 239000011541 reaction mixture Substances 0.000 description 5
• 239000007787 solid Substances 0.000 description 5
• 238000003756 stirring Methods 0.000 description 5
• NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 5
• 238000009736 wetting Methods 0.000 description 5
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
• 235000010469 Glycine max Nutrition 0.000 description 4
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
• 235000014676 Phragmites communis Nutrition 0.000 description 4
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
• 241000209140 Triticum Species 0.000 description 4
• 235000021307 Triticum Nutrition 0.000 description 4
• 239000008280 blood Substances 0.000 description 4
• 210000004369 blood Anatomy 0.000 description 4
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• 210000001061 forehead Anatomy 0.000 description 4
• 239000004615 ingredient Substances 0.000 description 4
• 230000005764 inhibitory process Effects 0.000 description 4
• LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
• 230000001473 noxious effect Effects 0.000 description 4
• 229910000027 potassium carbonate Inorganic materials 0.000 description 4
• 235000011181 potassium carbonates Nutrition 0.000 description 4
• 239000000243 solution Substances 0.000 description 4
• QQXLDOJGLXJCSE-KNVOCYPGSA-N tropinone Chemical compound C1C(=O)C[C@H]2CC[C@@H]1N2C QQXLDOJGLXJCSE-KNVOCYPGSA-N 0.000 description 4
• 244000300297 Amaranthus hybridus Species 0.000 description 3
• 235000004135 Amaranthus viridis Nutrition 0.000 description 3
• 240000002791 Brassica napus Species 0.000 description 3
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
• 244000068988 Glycine max Species 0.000 description 3
• 229910002651 NO3 Chemical class 0.000 description 3
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical class [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 3
• 229910019142 PO4 Inorganic materials 0.000 description 3
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical class [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
• 150000001340 alkali metals Chemical class 0.000 description 3
• 150000005215 alkyl ethers Chemical class 0.000 description 3
• 210000000481 breast Anatomy 0.000 description 3
• 239000012267 brine Substances 0.000 description 3
• 229910000019 calcium carbonate Inorganic materials 0.000 description 3
• 230000006378 damage Effects 0.000 description 3
• 239000012024 dehydrating agents‎ Substances 0.000 description 3
• USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 3
• 239000008187 granular material Substances 0.000 description 3
• 239000003621 irrigation water Substances 0.000 description 3
• NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
• 239000007800 oxidant agent Substances 0.000 description 3
• VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 3
• 239000010452 phosphate Substances 0.000 description 3
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
• 229910000029 sodium carbonate Inorganic materials 0.000 description 3
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
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• 150000003512 tertiary amines Chemical class 0.000 description 3
• 238000005406 washing Methods 0.000 description 3
• RUYYGKZODMTDJA-UHFFFAOYSA-N (2-methylpyrazol-3-yl) 3-(2-methoxyethoxy)-2-methyl-4-methylsulfonylbenzoate Chemical compound C1=C(S(C)(=O)=O)C(OCCOC)=C(C)C(C(=O)OC=2N(N=CC=2)C)=C1 RUYYGKZODMTDJA-UHFFFAOYSA-N 0.000 description 2
• 238000005160 1H NMR spectroscopy Methods 0.000 description 2
• IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 description 2
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• BKHMEXCHWYEXRR-UHFFFAOYSA-N 3-(2-methoxyethoxy)-2-methyl-4-methylsulfonylbenzoic acid Chemical compound COCCOC1=C(C)C(C(O)=O)=CC=C1S(C)(=O)=O BKHMEXCHWYEXRR-UHFFFAOYSA-N 0.000 description 2
• 239000005995 Aluminium silicate Substances 0.000 description 2
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• 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
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• 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
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• OTSAMNSACVKIOJ-UHFFFAOYSA-N azane;carbamoyl(ethoxy)phosphinic acid Chemical compound [NH4+].CCOP([O-])(=O)C(N)=O OTSAMNSACVKIOJ-UHFFFAOYSA-N 0.000 description 2
• AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
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• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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• 235000019438 castor oil Nutrition 0.000 description 2
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
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